1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-ethynyl-1H-imidazole-4-carbonitrile

ID: ALA4463936

Cas Number: 126004-13-5

PubChem CID: 11043123

Max Phase: Preclinical

Molecular Formula: C11H11N3O4

Molecular Weight: 249.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#Cc1c(C#N)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H11N3O4/c1-2-7-6(3-12)13-5-14(7)11-10(17)9(16)8(4-15)18-11/h1,5,8-11,15-17H,4H2/t8-,9-,10-,11-/m1/s1

Standard InChI Key:  OAMMFSMFVAEFOI-GWOFURMSSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   11.9153   -4.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7325   -4.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9868   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3239   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6651   -3.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2120   -4.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4341   -4.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8878   -3.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7176   -2.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7644   -3.3096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4244   -3.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0862   -3.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8348   -2.5341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0176   -2.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4231   -4.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4243   -5.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8606   -3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6375   -3.8188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  1  6
  1  7  1  6
  5  8  1  1
  8  9  1  0
  3 10  1  1
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 10  1  0
 11 15  1  0
 15 16  3  0
 17 18  3  0
 12 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4463936

   1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-YL]-5-ethynylimidazole-4-carbonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 249.23

Molecular Weight (Monoisotopic): 249.0750

AlogP: -1.65

#Rotatable Bonds: 2

Polar Surface Area: 111.53

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 0.59

CX LogP: -1.39

CX LogD: -1.39

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.54

Np Likeness Score: 0.69

References

1. Okano Y, Saito-Tarashima N, Kurosawa M, Iwabu A, Ota M, Watanabe T, Kato F, Hishiki T, Fujimuro M, Minakawa N..  (2019)  Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents.,  27  (11): [PMID:31003866] [10.1016/j.bmc.2019.04.015]

2. Nascimento IJDS, Santos-Júnior PFDS, Aquino TM, Araújo-Júnior JX, Silva-Júnior EFD..  (2021)  Insights on Dengue and Zika NS5 RNA-dependent RNA polymerase (RdRp) inhibitors.,  224  [PMID:34274831] [10.1016/j.ejmech.2021.113698]

Source

Source(1):

• Scientific Literature